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2-((tert-Butyldiphenylsilyl)oxy)acetic acid

Product Name
2-((tert-Butyldiphenylsilyl)oxy)acetic acid
CAS No.
76271-74-4
Chemical Name
2-((tert-Butyldiphenylsilyl)oxy)acetic acid
Synonyms
DKFELEX0341;2-((tert-Butyldiphenylsilyl)oxy);2-((tert-Butyldiphenylsilyl)oxy)acetic acid;Acetic acid, 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-
CBNumber
CB52693193
Molecular Formula
C18H22O3Si
Formula Weight
314.45
MOL File
76271-74-4.mol
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2-((tert-Butyldiphenylsilyl)oxy)acetic acid Property

Boiling point:
395.1±34.0 °C(Predicted)
Density 
1.10±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
pka
3.41±0.10(Predicted)
Appearance
Colorless to light yellow Oil
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Matrix Scientific
Product number
095009
Product name
2-((tert-Butyldiphenylsilyl)oxy)acetic acid
Purity
95+%
Packaging
250mg
Price
$742
Updated
2021/12/16
AK Scientific
Product number
1864AC
Product name
2-((tert-Butyldiphenylsilyl)oxy)aceticacid
Packaging
1g
Price
$978
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
ORS0003978
Product name
2-((TERT-BUTYLDIPHENYLSILYL)OXY)ACETIC ACID
Purity
95.00%
Packaging
250MG
Price
$1218
Updated
2021/12/16
Matrix Scientific
Product number
095009
Product name
2-((tert-Butyldiphenylsilyl)oxy)acetic acid
Purity
95+%
Packaging
1g
Price
$1647
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
ORS0003978
Product name
2-((TERT-BUTYLDIPHENYLSILYL)OXY)ACETIC ACID
Purity
95.00%
Packaging
5MG
Price
$497.5
Updated
2021/12/16
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2-((tert-Butyldiphenylsilyl)oxy)acetic acid Chemical Properties,Usage,Production

Uses

2-[(tert-Butyldiphenylsilyl)oxy]acetic Acid is an intermediate in the synthesis of N-Desmethyl-N-hydroxymethyl Tebuthiuron (D295445), a metabolite of the nonselective broad spectrum herbicide Tebuthiuron (T013620).

Synthesis

154698-92-7

76271-74-4

The general procedure for the synthesis of 2-((tert-butyldiphenylsilyl)oxy)acetic acid from methyl 2-((tert-butyldiphenylmethylsilyl)oxy)acetic acid was as follows: to a solution of methyl 2-((tert-butyldiphenylsilyl)oxy)acetic acid (8.86 g, 27.0 mmol) in THF/H2O (4:1, 33 mL) was added an aqueous 0.75 M LiOH solution ( 97 mL, 72.9 mmol). The reaction mixture was stirred at room temperature until thin layer chromatography (TLC) showed complete consumption of the feedstock. Upon completion of the reaction, water (appropriate amount) was added and the resulting mixture was extracted with ether (3 x 40 mL) to remove non-acidic impurities. The aqueous phase was acidified to pH 3 with 10% aqueous HCl and subsequently extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was confirmed for purity by nuclear magnetic resonance (NMR), which resulted in 2-((tert-butyldiphenylmethylsilyl)oxy)acetic acid (7.97 g, 94% yield) as a colorless oil. The structure of the product was determined by 1H NMR (400 MHz, CDCl3): δ 7.68-7.65 (m, 4H), 7.46-7.38 (m, 6H), 4.25 (s, 2H), 1.10 (s, 9H); 13C NMR (100 MHz, CDCl3): δ 174.9,135.5,132.9,130.2. 128.0,61.9,26.7,19.2; mass spectrum (M/z): 237.1 (M+-Ph); Fourier Transform Infrared Spectroscopy (FT-IR, thin film): 1737 cm-1 (C=O telescoping vibration); Calculated values for elemental analysis (%): C, 68.75; H, 7.05; Measured values (%): C, 68.70; H, 6.91.

References

[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 3, p. 1236 - 1241
[2] Journal of the American Chemical Society, 2010, vol. 132, # 31, p. 10920 - 10934

2-((tert-Butyldiphenylsilyl)oxy)acetic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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2-((tert-Butyldiphenylsilyl)oxy)acetic acid Suppliers

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76271-74-4, 2-((tert-Butyldiphenylsilyl)oxy)acetic acidRelated Search:


  • 2-((tert-Butyldiphenylsilyl)oxy)acetic acid
  • Acetic acid, 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-
  • 2-((tert-Butyldiphenylsilyl)oxy)
  • DKFELEX0341
  • 76271-74-4